Hydrofluoroether compounds (HFEs) comprise a class of commercially valuable chemical compounds. In a number of applications, hydrofluoroethers have been found to be useful as replacements for chlorofluorocarbons (CFCs), which are currently disfavored and regulated due to the adverse effects that CFCs are believed to have on the environment. Unlike CFCs, hydrofluoroether compounds that contain fluorine as the only halogen have essentially no effect on the earth's ozone layer. Such hydrofluoroether compounds are thus said to exhibit an “ozone depletion potential” of zero. In addition, such HFEs are typically more easily degraded within the earth's atmosphere, which results in a low global warming potential.
Hydrofluoroether compounds have been prepared by various different methods including, for example, alkylation of perfluorinated acid fluorides (prepared by electrochemical fluorination or by direct fluorination), alkylation of perfluorinated ketones (prepared by reaction of perfluorinated acid fluorides and perfluorinated olefins), and photooxidation of tetrafluoroethylene (TFE) followed by reductive stabilization. Such methods have various advantages and disadvantages. For example, the latter method requires the handling of a relatively hazardous reagent, TFE, and also provides a broad product mixture that generally requires extensive purification. Such methods also have generally not been suitable for the direct formation of cyclic HFEs (that is, for the formation of a ring structure during an alkylation step).